Youth unemployment rates in most countries are considerably higher than total unemployment rates and increased significantly in many countries following the global financial crisis. Young people in long-term unemployment risk becoming a ‘lost generation’. We investigate individual and family characteristics predicting young people’s vulnerability to the scarring effects of long-term unemployment. After overviewing aggregate youth unemployment trends in several European countries, we focus on Russia and Italy – countries with contrasting structural and institutional conditions and exhibiting different macroeconomic trends – in order to determine whether, despite these differences, there were similar patterns in the relationship between individual and family characteristics and the of risk of unemployment and its adverse impacts. We use a Heckman probit model to estimate the unemployment risk of young people – compared to adults – during the period 2004–2011, before and after the global financial crisis. Despite many differences between the two countries, most of the explanatory variables acted in the same direction in each and so we compare the relative size of such effects. The policy significance of the findings is that personal and family characteristics are more amenable to modification than macroeconomic variables. Specific school-to-work interventions are needed to avoid creating a ‘lost generation’.